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Volumn 35, Issue 3, 2011, Pages 581-586

Synthetic approaches to selenacephams and selenacephems via a cleavage of diselenide and selenium anion

Author keywords

[No Author keywords available]

Indexed keywords

ANION; AZETIDINONE DERIVATIVE; SELENIUM;

EID: 79952226525     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/c0nj00782j     Document Type: Article
Times cited : (18)

References (43)
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    • A. Krief, in Comprehensive Organometallic Chemistry, ed., W. W. Abel,,, F. G. A. Stone, and, G. Wilkinson,, Pergamon, Oxford, 1995, vol. 11, p. 515
    • (1995) Comprehensive Organometallic Chemistry, Ed.
    • Krief In, A.1
  • 10
    • 0000709738 scopus 로고    scopus 로고
    • T. Wirth Angew. Chem. 2000 112 3890 Angew. Chem., Int. Ed. 2000 39 3740
    • (2000) Angew. Chem. , vol.112 , pp. 3890
    • Wirth, T.1
  • 11
    • 77955170036 scopus 로고    scopus 로고
    • A. R. Katritzky, C. A. Ramsden, F. V. Scriven and J. K. Taylor, Elsevier, Oxford
    • Comprehensive Heterocyclic Chemistry III, ed., A. R. Katritzky,,, C. A. Ramsden,,, F. V. Scriven, and, J. K.,, Taylor,, Elsevier, Oxford, 2008
    • (2008) Comprehensive Heterocyclic Chemistry III, Ed.
  • 35
    • 77951780812 scopus 로고    scopus 로고
    • 2-(Trimethylsilyl)ethaneselenol was prepared from its diselenide and used for the preparation of ammonium aromatic diselenoates. See:
    • D. B. Bankar M. Koketsu Eur. J. Org. Chem. 2010 2742
    • (2010) Eur. J. Org. Chem. , pp. 2742
    • Bankar, D.B.1    Koketsu, M.2
  • 39
    • 0000687399 scopus 로고
    • It is well known that N-unsubstituted β-lactams carrying a 4-acetoxy residue at C-4 (in compound 3) react with nucleophiles to afford the product with complete retention of configuration. The reason for that resides in the fact that compounds like 3 in the presence of a base undergo elimination of acetic acid to form an intermediate imine species that reacts with nucleophile from the less hindered side of the azetidinone ring to afford trans β-lactams, thus with a retention of configuration. For selected references see:
    • S. Murahashi T. Naota T. Kuwabara T. Saito H. Kumobayashi S. Akutagawa J. Am. Chem. Soc. 1990 112 7820
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7820
    • Murahashi, S.1    Naota, T.2    Kuwabara, T.3    Saito, T.4    Kumobayashi, H.5    Akutagawa, S.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.